what game are you playing?

Some thoughts on work, ambition, and making it out the hood

I.

At a retreat, someone asks me:

“Do you treat your life as a game or are you just doing your own thing?”

“Definitely my own thing”, I answer.

I’m watching the sunset over a ranch that’s nice enough to host a celebrity wedding, eating steak and exotic honey paid for by the LPs, in a room with 100 brilliant young people using their talents to get people more addicted to their phones, and all I can think about is how I’m just a kid from Scarborough, Ontario.

How the hell did I make it here?

I’ve spent most of my 20s in San Francisco. To even be able to live here is an accomplishment to my parents’ friends. Almost every single person I meet here was the best in their town at coding/tech/startups, and just wanted to move to place where people get it. That’s how it starts, the dream itself is living here.

Once you’re here for a few years, you forget that you used to pray for days like this. Perfect weather, jobs that grow on trees, friends within a 15 minute walk and events every weekend. It’s more impressive to have a girlfriend than it is to raise 5 million dollars here.

The thing about everyone having money is that most people who have it, grew up having it. Quitting your job to do a startup is a lot easier when your dad was a VP at Apple. We’re all jumping out of planes but only some of us have parachutes. We’re all in the same room, but some of us were born in a ballroom, and some of us (me) don’t know why there’s 3 forks around our plates.

II.

“What are you optimizing for?” the same person asks me.

“I dunno. I just like what I do.”

I thought it was money at first. I started a dropshipping business in high school and quickly made enough to pay for (Canadian) college. If I really was money-maxxing, I would have ran it for more than 4 months. I shut it down after I got bored. I didn’t feel like I was learning anything watching this business chug along. The money wasn’t really hitting.

A lot of my family’s problems settled after we got more money. But at 19, I was in the 99th percentile of annual income in Canada for 30-40 year olds, and I was still riddled with insecurities and loneliness. I had a feeling that probably wasn’t the way, but I didn’t really know what was, and money seemed important. So while I didn’t see the point in having so much money, I still made pretty fiscally sound moves.

At a certain point I thought I just wanted to learn everything. Read every book, become a CTO level engineer, become really interesting to everyone I met. Knowledge-maxxing — I loved feeling smart and being right. I kinda fell into the Good Will Hunting trap where there wasn’t much I could tell anyone they couldn’t read in some fucking book. I cared more about being right than I did about learning. I couldn’t handle looking dumb which put a cap to how much I could learn. I wasn’t okay with the fact that you can only learn something by being wrong or clueless about it initially.

Maybe being a brainiac just wasn’t my game. Maybe I needed to friend-maxx. Lean into my social proclivities and become a super networker. But not like the other networkers, more genuine. But also so I can sell them GPUs and use my friendliness productively somehow. I had to cash in on these connections somehow, or else what was the point? Dammit, I wish I’d become friends with more AI founders. Don’t be transactional, but also don’t spend too much time with other people. Your laptop will miss you if you spend too many weekends away.

III.

“Why are you here?” I wonder as I stare at all the people in the foyer. I wonder the same about myself. I tell myself it’s for the visa, but they already signed my letter. I could’ve just said no if I knew it’d sap my time and energy.

I think I’ve been at odds about my own ambition for a while. I pride myself on my honesty yet I can’t honestly answer simple questions like “why do you do what you do?” I still can’t. There’s no root cause analysis, just the feeling that it’s the most right thing I’ve ever done.

When I quit my last job, I was trying to explain to my CTO why I was leaving. I gave a bunch of reasons, he rightfully pushed back, and in the end I admitted it’s just a feeling and I have to do it. “I don’t know what I want to do, but it’s not this,” I remember thinking. After realizing that, I accepted that any more time I spent there was a waste. It’s like realizing you don’t want to marry someone yet continuing to date them. There’s the sharp pain of ending something, and the slow throbbing pain of choosing to stick with something you know isn’t for you. There’s pain on both sides, pick one.

I’ve recently become okay with introducing myself as a writer. There’s no formal qualification for it, but I think I’ve come up with one that works for any identity. I’ve realized that if I don’t write for too many days in a row, it starts to hurt. Like a sinus infection or constipation, there’s too much in my brain that needs to be taken out.

There’s no point where I’ll be done with writing. There’s no single point in the future where I’ll have accomplished everything I’ll have wanted to, then I’m just fine for the rest of my life, because no matter how much I poop, I’ll have to poop again someday. I give up every single sentence I have to the world, knowing that it’ll help me come up with more sentences, and it’ll only stop if one day I bear the pain of constipation. It hurts to write, to go through 6 drafts and only then feel like it’s beautiful enough to share, but it hurts more to keep it all inside.

I came here because I wanted to meet other people who knows what that’s like. I wanted to validate my own identity as someone who makes things by cross-checking with other people. Do you feel the same way when you can see the piece in your head and you can’t rip yourself away from the screen til your creation matches your vision? Do you also feel like you could create for weeks and feel like you’ve made no progress til it all comes together? Do you also feel your 16 year old self trapped inside you crying and laughing and being scared and bored, and do you also do it all for him?

I don’t care how much he raised or what her total comp is. I don’t care about this brand deal or that launch video. Ironically my favourite question is “What would you do if AGI solved everything, scarcity included?” But no one can see past escaping the permanent underclass. What would you do if it couldn’t be a business? What would young-you be happy seeing you do? Are you living the dreams you set out for yourself years ago, and if so, does it feel like it? Are you looking for an answer, and what’ll you do when you find it? I ask myself these questions constantly, and often I have no answers because it’s scary to feel dumb and not know things.

So I tell myself, in rooms full of talented people where I’m a little nervous and very excited and maybe a bit insecure:

• be curious, not judgemental

• you can’t know something if you haven’t been taught

• everybody poops

Then I try my best to listen as much as possible, and remember that no one thinks too much about the random 10 minute conversations we have, and we will all die one day. Better to just try and do what you want before you can’t anymore.